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The development of a novel intermolecular oxidative amination reaction, a synthetic transformation that involves the simultaneous functionalization of both a N-H and C-H bond, is described. The process, which is mediated by an I(III) oxidant and contains no metal catalysts, provides a rapid and green method for synthesizing protected anilines from simple… (More)
The most direct method for synthesizing 2-arylindoles is oxidative coupling of an arene with an indole. We have shown that both the activity and regioselectivity of this cross-coupling reaction are correlated with the acidity of the medium. This insight has been applied to predict the best conditions for the oxidative cross-coupling of N-alkylindoles, an… (More)
A novel variation of the rhodium catalyzed [4 + 2] reaction is reported. A catalyst system that forms an eight-membered ring product from the incorporation of an alkyne into a dienyne is discussed. The products are formed with high diastereoselectivity and in good yield. The highest yields are obtained with alkynes that possess either an oxygen or nitrogen… (More)
A modern apparatus for performing flash chromatography using commercially available, prepacked silica cartridges has been developed. The key advantage of this system, when compared to traditional flash chromatography, is its use of commercially available silica cartridges, which obviates the need for students to handle silica gel. The apparatus has been… (More)
N-Acetylindoles can be oxidatively coupled with arenes such as benzene or pentafluorobenzene in dioxane. The use of Cu(OAc)(2) as the stoichiometric oxidant produces selective arylation at the 3-position of indole while AgOAc produces selective arylation at indole's 2-position.
We herein present a new oxidative cyclization of alkene-amide substrates under neutral and catalytic conditions. This overall transformation requires tandem sp3 C-H activation (at the position adjacent to the amide nitrogen) and C-C bond formation. Specifically, pyrrolidine 1 was converted to pyrrolizidinone 3 and indolizidinone 4 in 66% and 17% yield,… (More)
Electron poor benzimidazole substrates were arylated via an intramolecular cross-dehydrogenative coupling (CDC) reaction. These CDC reactions were catalyzed by a Pd(II)/Cu(I) catalyst system, capable of producing moderate yields on a large library of substrates. The substrate scope consisted of tethered arene-benzimidazoles that upon coupling, produced a… (More)
The vanadium-catalyzed oxidative coupling of substituted 2-arylimidiazo[1,2-a]pyridines to N-methylmorpholine oxide, which acts as both a coupling partner and an oxidant, has been achieved. This reaction was applied to various substituted imidiazo[1,2-a]pyridine and indole substrates, resulting in yields as high as 90%. Mechanistic investigations indicate… (More)
S ince publishing our original manuscript, a few errors have been brought to our attention. The references in Scheme 1 were inverted. A corrected scheme is shown below. Additionally , the text accompanying Table 3 refers to the substrate as a 3-methylthiophene; it is actually a 4-methylthiophene. Finally, two names were misspelled in the references section.… (More)
A new approach for the direct amination of 2-phenylpyridine derivatives using a diphthalimide-iodane and copper triflate has been developed. A series of different 2-phenylpyridine derivatives were aminated with yields up to 88%. Mechanistic investigations indicate that the reaction proceeds via a copper-mediated single electron transfer.